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Synfacts 2007(12): 1262-1262  
DOI: 10.1055/s-2007-991365
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Boron-Based Acenes

Contributor(s): Timothy M. Swager, Trisha L. Andrew
T. Agou, J. Kobayashi, T. Kawashima*
The University of Tokyo, Japan
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

A general procedure to synthesize anthracene- and pentacene-type azaborine hetero­cycles was developed. Dibrominated derivatives (e.g., 1) were also synthesized in high yield (>95%) following the same procedure and were found to be stable to both subsequent lithiation and palladium-catalyzed cross-coupling reactions. Carbazole-functionalized azaborines, such as 2, display fluorescence quantum yields close to unity and efficient energy transfer from the carbazole moiety to the azaborine skeleton.